Why You Should Freelance (Despite All That Face-Punching Business)


My name is Chuck, and I remain a freelance penmonkey.

Yes, freelancing is a lot like punching yourself in the face. Over and over — and over — again. Sometimes, I feel like that animated GIF where the chimpanzee pees in his own mouth.

And yet? Here I am. Freelancing my heart out. And my pants off. No, seriously: I still haven’t put on any pants. By golly, I don’t have to. You keep your oppressive pants regime to yourself, pal. I’m fancy-free.

You want to know the other side? The not-so-sucky and sometimes downright lovely side of freelancing? It isn’t all one big masochist’s parade, after all. Fine. I can do that.

Here’s why you want to freelance despite all the self-inflicted misery:

Because You Can Watch Baby Deer Frolic From Your Office Window

I’m at a desk. The desk faces two windows. Beyond these two windows waits the forest surrounding Der Wendighaus v2.0 (yes, I have a cult-like compound in the woods, shut up). And in those woods lurk whitetail deer and their little fawn babies. I’ve seen ’em. They frolic and gambol about, and sometimes I think, “Those deer? Those deer are freelance.” Because sometimes being here, working out of the home office, that’s how I feel. Yes, I’m smashing my nose against the grindstone (so hard I’m sometimes afraid it’ll be sanded off, bzzt), but I also have ludicrous amounts of freedom in how I approach my day. The things you can’t do at your day job? I can do those things here. Crank music. Read a book for research. Drink an adult beverage. Cook myself an egg sandwich. Have long conversations with stupid dogs. I feel like the deer outside my window — dancing through the trees, taking whatever path best suits their whims.

Because Cubicles Are Like Little Prisons

I have been in many-a-cubicle. They are, regardless of their shape or construction, like little Guantanamos, little Alcatrazes. Oh, those awful gray walls forever covered in a light pubic fuzz, as if they have been covered in the pelt of some depressed Muppet. You peer out over the edge, beyond the proscribed borders — the DMZ of other desks, other 9-t0-5ers (which sounds an awful lot like other lifers) — and it’s just a sea of assholes, each trying to convince the world they’re really working when really they’re just watching nutso shit on the Internet. You know what we did with the office here? We painted it green. Crazy green. Like, dip a Granny Smith apple in a tub of uranium, then paint the liquefied fruity radioactive remains on the walls. You think you’ll get that color on your cubicle? Good luck. They’ll shoot you. Or worse, “write you up.” Someone who shall remain nameless (though her title rhymes with “Pie Strife”) works at a job where they’re moving offices, and at the new offices, the “open concept” is beyond Draconian. No pictures. No plants. No fans. No trash can. No papers on your desk. You can almost hear the clatter of keys in a lock.

Because, You Know What? Fuck The Boss

I’ve had a couple good — even great — bosses. But a lot of them were real asshats. Middle management floaters, often unaware of what those beneath them actually do, and ignorant enough that they’ve reached the pinnacles of their pbbt-thbbt mediocre careers. A lot of them micro-manage, too, which is about as much fun as a proctological exam performed by an epileptic with large, callused hands. You know who micro-manages me? Me. You know who is the boss of me? Me! Nobody else. Yes, I have clients, and yes, it is my job to meet the needs of those clients. But even the worst client is better than the best boss. You know why? That client isn’t here. He’s not standing over your shoulder. He doesn’t need a bullshit mug from you on some kind of bullshit Appreciate Your Asshole Boss Day. You don’t have to feel guilty when a client walks by your desk and you’re watching some crunchy dude in the woods go moonbat over a double rainbow. And the client will move on. You’ll have other clients. You are not slave to a single master.

Because Once In A Blue Moon, You Get To Feel Like A Goddamn Rock Star

Yesterday, we had a guy come out to look at the jury-rigged radon setup in the basement of the new house, and when I told him what I did for a living, he suddenly got very interested. What do you write? Have I read it? Do you like it? That sounds incredible. Once in a while, you’ll tell someone what you do — “I’m a freelance writer” — and they’ll get this look in their eyes like they’re looking at a crazy person. But not a dangerously crazy person — no, they see you as one of those dudes who went off the reservation to live off the grid. They look at you like you escaped. Like you tore open your straitjacket and kicked down the asylum door and ran into the woods, hooting and gibbering a hymn to sweet freedom. (See, that’s the secret: those people who pretend that freelancing isn’t a real job? Pshh, they’re just jealous.) And sometimes, sometimes you encounter someone who genuinely respects what you do, and maybe is even familiar with your work. That’s when you get a rockstar moment and it all feels really worth it.

Because You Are Like A Mutant Radiation Wolf: Hunter And Survivor

Take a look outside. No, no, look past the frolicking deer and the gibbering , hooting freelancer. What do you see? What I see is an economy that continues to try to get up out of the bed, but instead of escaping the bed all it does is defecate and throw up on itself. I see layoffs. I see rising unemployment. I see those who do have jobs made to suck a bigger pipe every day — no raises, no bonuses, health insurance costs going through the ceiling, smaller offices, shrinking cubicles, leashes tighter and tighter until one’s cheeks turn blue. It’s the apocalypse out there, folks. The freelancer, though? The freelancer isn’t a big yacht that can’t turn its ass around. The freelancer is a little boat with a big engine zig-zagging all over the place like a coke-addled water skeeter. You can turn on a dime. Big companies — and those in the belly of big companies — cannot. Freelancers adapt. One line of work dries up? Find another. Yes, you must forever be the hunter, but that means you’re a survivor, too.

Because The Tax Deductions Are Pretty Sweet

It’s a small point, but a fun one. As a writer who writes books, film, games, etc — I can buy stuff because I need it. And if I need it? I can possibly deduct it. It has limits, but I gotta tell you — when tax time comes around, it’s hard not to feel satisfied when you deduct books, games, travel.

Because You Can Get Really Good At It

If you approach it like a business? If you approach it with discipline? If you don’t spend all day drinking vodka from the bottle and rolling around in your own filth? Then hot damn, you can get pretty good at it. And you can make a living, too. And you can do it without killing yourself provided you’re willing to spend a little time on techniques to improve efficiency (again, you have to treat this like a business because, well, it is a business). When it comes time that freelance puts food in your mouth and a roof over your head, well, it doesn’t get much sweeter than that. It is the salve that heals the cuts and bruises from all that fucking face-punching. Now if you’ll excuse me, I have to go punch myself in the face and get some work done.


  • As true as your post yesterday might have rung, this one just rings louder in my head. Right now, going completely freelance is my goal, so I enjoy thinking of what you have built for yourself already.

    I have enacted my own 5-year-plan and am well on my way. Which basically just means I work all day and then come home and work all night. But the goal is clear: being pantless and frolicking with dear. Thanks for articulating that!

  • You forgot one…THE MONEY! Oh, the sweet, sweet money.

    I may be one of the lucky ones, but my income tripled when I went freelance. Why? All that profit the company needed to pay my useless boss, my inept coworkers, the non-functional mail room, all those fluorescent lights, the cleaning service, the rent on the big fancy show building, the excessive executive salaries, etc., etc., etc? It’s mine! All mine!!! [cue wild dancing and frolicking with aforementioned deer]

    Sure, I pay for a lot of stuff they may have begrudgingly paid for ten, but the costs do not outweigh the fiscal benefits, not by a mile.

    And, to your note about no vacations…true. But with a blackberry/iphone, my ipad, 3G and wifi, I can also work from a beach in bora bora as easily as a client office as easily as a cabin in the adirondacks. So, the family vacations, I put in a few hours, and join them.

    • @Mike:

      I don’t know that my income tripled, but it stayed relatively the same — and brought a lot more personal pleasure with it.

      As for the vacation, one thing worth mentioning is that the flip-side is true. While you get “paid vacations” from a day job, you’re bound to the schedule of the company and your “alloted” time — whether to be on a beach or sick in bed. Freelancers have the freedom to rearrange time as they see fit, which has its own sugary-sweet flavor.

      — c.

  • Hey, you forgot security. I know, I know. You’re all thinking, “Whoa there, chucklepants. Security? That’s real-job stuff there, boyo.” And maybe once upon a time it was. Maybe once having a real job meant at least you HAD a job. But take a look at the unemployment numbers. Even when Arthur Andersen went BOOM and took 55% of my freelance revenue with it, that left 45%. Lose your real job and you lose all of it. I still had five other regular clients and a handful of contacts that were good for the occassional bit o’ work here and there, and I was able to cobble that sad confederacy into almost three years of hanging on until I got a day job offer that was just too good to refuse.

    So yeah, security. And a lesson learned. Diversify your client base. Don’t let any one of them get to be 55% of your cash flow.


  • This post and yesterday’s strikes a great balance, and makes me salivate as I think of the day when I can tie my metaphorical bedsheets together and leap from the corporate walls into the dark churning bay waters of freedom.

    It’s why I’m trying to write posts earlier in the day, to make more time on my lunch breaks for editing the manuscript. I’m sorting out dragons to chase. Sharpening my sword, or rather the mightier pen. Because if I want to get out of this life, I’m gonna have to fight.

    Once that fight’s done, punching myself in the face might actually seem like a luxury.

  • Awwwww yeah. One of the unsung benefits of the freelancer: LUNCH! A foodie’s dream, man. Me and my CSA veggies and my whole kitchen at my disposal. No more relentless routine of Taco Bell and skeevy Chinese places for me.

    Dan O’Shea, you are wise, and I wish I could’ve heard you say that sooner. Until recently, I only ever took one contract at a time — an ARG takes up a huge mental footprint, and I wasn’t sure I could manage two at once. But that leaves you with gaps between games it’s hard to fill.

    Lately I’m doing a bunch of contracts at once, though. It’s… not as hard as I expected. Of course, none of ’em are true full-blown ARGs, either.

    • @Andrea, Dan —

      Yeah, no doubt. Most of my freelance life was 70-80% of my workload for many, many years (ahem, White Wolf), and they’ve pulled back from such heavy game publication, which left me with a startling gap. I filled it, but it took a little time (and a little panic).

      — c.

  • The one thing I miss the most: impressing people with my job title. And I really, really, really miss that. “My dad’s a writer,” my son would say. “He’s free pants.”

    God, I miss that.

  • Fantastic balance between the two posts. I don’t really have that much to add to it myself, not having sold a single word yet. Although I am trying to change that in the near future.

    Part of me is afraid though. I have that pesky second-language barrier that I need to overcome. Not just in terms of using or understanding the language, that’s all good. Or at least, I believe that’s all good. My main issue tends to be confidence. Going to England for a bit over a week made me more confident, but I’m not convinced until the day I exchange words for coins, bills, or even digital money.

    Sure, I can try the market here in the Netherlands. It’s a much smaller market. One that’s not really taken seriously. Filled with people who will get the job because they’re well known. Not because they’re writers, but because they’ve done other stuff.

  • Right now, the benefits are intangible…but awesome.

    The highlight of my career so far – seeing my name under that big sexy Star Wars logo. It triggered an addiction I didn’t know I had. I want to see it there again…and again….

  • And now my day has been made better, and my writing optimism has returned. You, sir, are a god among men.

    When I become a full-time freelancer, I shall build a shrine in your honour out of baby deer and dance pantsless upon it.

  • What Josh said. =)

    At the end of the day, there are pros and cons to everything you choose to do in life. Many people dismiss the intangibles like happiness, stress level, and freedom.

    Everyone has to find the balance that works for them. For some it swings to a day job. For others, freelancing is the path to take.

    I haven’t tested the freelance side of life, but I hope to try one day. If it works out, great! If not, there’s always some corporate asshat that needs another douchebag programmer. =D

  • For me the best thing about freelance translation would be: “you get to learn EVERYTHING and meet EVERYONE”. They need you to translate heart medicine leaflets? Get ready to meet a REAL doctor and learn a whole boatload about cardiology. A book about race cars? Now you now what a monocoque is and how to change your break pads.

  • Chuck, your posts are absolutely brilliant!! You’ve validated the pros/cons of the freelancing life so well that I’ve been compelled to read them a few times… because they feel just ‘that’ good. I’ve also passed them along on FB. Bless you!

  • All these reasons – and yesterday’s – apply to me as someone who’s trying to do more and more freelancing.

    But the bigger reason that I freelance, and it’s a good thing, is that I don’t have many other choices. I’m bad at marketing myself or my blog, so if I want to write about the things I want to write about and have them read, I have to freelance. And I have written, and it’s been read, and it’s awesome.

    Still waiting on some of those checks, though….

  • Love both entries. As a freelance illustrator, I’ve been happy to come home from a long day of working to a long evening of working. I’m one of the people in the world who has a dull, if nearly stress-free day job. Another big point to consider when being a freelancer is making sure you give yourself ONE day off a week to recharge.

    I sure put mine to good use.

  • I have really enjoyed these couple of posts. They accurately sum up a lot of my experiences as a freelance illustrator.

    I thought today’s hunter/survivor analogy to be a good one. I remember reading an anthropology book by Crhistopher Turnbull were he dismissed the notion that the farmer/setller always wins out over the hunter/gatherer. If a harvest fails the former is doomed, whilst the latter moves on to the next site and a different crop/game that may have thrived in those conditions.

    Personally I think the pros of freelancing massively outweigh the cons. Oh, and I live in the UK so I don’t have the health insurance issues either.

  • Yep, you got the pros of freelancing right too. There are two other benefits that come to mind: one, the freedom to make appointments and run errands while the rest of the employed masses are stuck in their cubicles. I have my own personal gym at 2:45 pm, instead of having to fight with people over the cardio machines at 6:30 pm. Grocery shopping and doctors’ appointments are easy to schedule; I don’t have to ask the boss for time off to go get my teeth cleaned.

    The second advantage is eating at home most of the time. For people like me who sport the freelancer-figure, who are now trying to repair the damage done by sitting at a desk for 80,000 hours, it’s a whole lot easier to cut back on calories AND save a wad of money by not eating out for breakfast, lunch, and/or coffee on a regular basis.

  • Great articles both! Having just come off a freelancing QA gig that sorta fell in my lap, and experiencing the joy of working with a great creative team, and watching our project launch and be enjoyed by others – it was a complete RUSH, and one I look forward to experiencing again, SOON.

    However, unless the “QA For Hire” stuff goes *really REALLY* well, I don’t see me giving up my day job anytime soon. My spouse is an unemployed IT Helpdesk/Network guy who’s been attempting to get a freelance thing going, but has only managed to wrangle one client. The problem there is ‘marketing’ (or lack thereof) and I’ve been considering trying to be the marketer, for both him and myself – but until we either have more clientele, or day job for the spouse, *my* day job pays the mortgage and health insurance and the hole-surrounded-by-flesh-into-which-one-pours-money teenage daughter.

    In the meantime while I attempt to play in both worlds, what would be cool is a “place” – forum or what-have-you – where freelancers can seek out advice, company, commiseration, or even networking, from/with other freelancers. Not so much the “hey you’re successful, can you send some clients my way” but more like “what system do you use to organize your work”, or “what do you use to track your time per client”, or “here’s my new site, what do you think?”. But best, to have conversations like the ones your past two posts have generated 🙂

  • I freelanced from 2003-2008, then took a day job with almost all the benefits (say 90% flexibility in terms of setting my own hours, and 90% of my work was from home), and a very good monthly paycheque. I was let go this spring, and though I certainly miss the paycheque, and though my colleagues and bosses were lovely, I am so much happier now I have my freedom again.

  • I’ve been freelancing (both illustrating and writing) for the last 7 years or so, but I also have a day job that’s flexible enough to let me work from home. Unfortunately my day job doesn’t pay as much and I don’t get enough freelance assignment for me to be really proud of my freelance work, especially with a wife and a kid.

    But somehow, I still feel satisfied with whatever illustration work that comes my way, much more than any other work I’ve done.

  • One thing I will say, having been a freelancer and not being so now: as a freelancer you begin to get very, very competent at doing lots of things. Personal development goes through the roof. Things I thought elementary when I was doing them by myself are now, it seems, my secret magical preserve in the office.

  • Umm so yeah, I found this blog post from my Twitter feed. Yesterday’s too (about face-punching) and I really enjoyed them. So much so I wasn’t a bounce (haha, SEO *cough*) and I toodled around your site.

    Holy crap you write for WHITE WOLF!

    Well count this lady and her man as fans and feel a little rock star love.

    One day I’d love to do internal illos for White Wolf someday. Vampire: The Masquerade is particularly close to my heart.

    You’ve earned yourself a solid follower here. Thanks for the great site. 🙂

  • I’ve always seen the choice as being a temperament thing.

    I have friends who absolutely turn white when I tell them that I can receive a call at any moment from someone I don’t know, telling me that I must work round the clock for the next 72 hours, pulling creative solutions out of my ass the whole way. But I’ve found that I thrive on those crisis scenarios.

    What I can’t deal with is showing up at the same place at 9am five days a week, to do the same work with the same people. Every time I try to work a day job, the allure of the hunter’s life is just too overwhelming.

    I’m just a terminal freelancer. I think of it as being an outside cat.

  • Can’t agree with this more! For me it also means not having to pay some stranger $800 a month to watch my son. Instead I can raise him myself. I can also have time to take him to do things like go to the park, go fishing, run my errands, and bake, cook, and do housework, all while additionally earning an income. For me I make less than I did working full time, but I also don’t devote 100% of my time to freelancing. I consider my freelancing part time because realistically I usually only work 5 – 15 hrs a week. But it’s a sacrifice I’m willing to make for happiness, freedom, and the ability to raise my own child. He did a month in preschool when I took on a temp job and he was always getting sick. I’m of an old school mentality and believe a child needs to grow with the security of their parents in order to learn to become an independent adult. I’ve done my time in “the office” and I’m sick of the politics, necessary ass kissing, and micro management. I’m from the world where hard work pays off and was getting nowhere in the corporate world because I refused to play their games. Instead, I gave myself a raise yesterday and it felt good. Thanks for reminding me of the pros and cons of freelancing and why I do it! And for making me get a good laugh too! We freelancers are the rockstars everyone wants to be!

  • This goes down as the most awesome thing I have EVER read. I’ve been running my business for four years now, but full-time for three. I tell my husband I have a love-hate relationship with it. One day it’s like I got karate-kicked in the face, and the next day I am the happiest girl on earth. Whenever I have a down moment, I am going to read this—because it’s a hilarious reminder of why I started this adventure and made me laugh so hard I cried. Five times. I want a poster of this so I can hang it on my wall. It’s my new mantra.

  • One word of caution. That tax deduction thing can be a trap. Buy something you don’t need for 30% or so off? That is still 70$ of the price you should not have spent in the first place. The key is to buy what you need, so you actually pocket the tax deduction. Also, you have to really save for tax time. Don’t be surprised when tax time comes around and you needed to have money stashed away for the government so they can build roads. Make your quarterly payments and track invoices and the likely tax payment (with a bit extra) religiously. You will be praying at the end if you don’t!

  • One thing -from my own experience- that didn’t get mentioned explicitely, or I must have overread it: you are doing something you love. You choose to do it, because you like it. And you make a living off of it. You aren’t stuck for the rest of your life in a day job that you secretly hate. You aren’t stuck with a profession you once learned out of some compromise with life and its circumstances while you really wished you had done something totally different. You have a talent, maybe a hobby, and you’re making money with it. Sometimes it doesn’t even feel like “work”, let alone like a “job” (and yeah, at other times it does). Of course that’s all part of the whole “freedom” and “your own boss” equation, but it really comes down to being its own factor. You’re doing something you love. “Regularly employed” people might sit in their cubicles and offices, realizing (or worse, not even realizing) how much they hate their job and the monotony and everything else about it. But I know of no fellow freelancers who’d secretly wish for a 9-to-5 at a bank or in an office. Because we’ve already broken down that asylum door and ran off into the woods, etc.

  • I love this post! Writer, indeed you are, Sir!

    I like your last reason the best. How else am I going to find my “voice” or “aesthetic” unless I’m left to my own devices? With imminent fear of death, and all that jazz.

    Yesterday I decided to become a freelance web designer/developer. And all your face-punching, balanced with baby deer, gives me courage!

    I look forward to reading more of your prose 🙂

  • “Yes, freelancing is a lot like punching yourself in the face.” Haha. That was a funny way to start off, but these are some great reasons. Thanks for this.

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